


Practice Makes Perfect

by Major_Fortune



Series: Widojest Smut [1]
Category: Critical Role (Web Series)
Genre: Caleb is into it, Dom/sub Undertones, F/M, First Kiss, Hand Jobs, Jester has a sub side, Mutual Pining, Plot What Plot/Porn Without Plot, Roleplay, Tails, Teacher/Student Roleplay, Vaginal Fingering, Virginity, ok some plot
Language: English
Status: Completed
Published: 2019-07-02
Updated: 2019-07-02
Packaged: 2020-06-02 13:49:38
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,338
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19442704
Author URL: https://archiveofourown.org/users/Major_Fortune/pseuds/Major_Fortune
Summary: Jester always makes sexual jokes, it’s part of her charm, that and drawing very intricate... members. But when Caleb answers to one of her inappropriate jests with way too much honesty, she can’t help but blush. Now she can’t stop wondering about how sexually experienced the wizard is and if maybe he could teach her a thing or two...





	Practice Makes Perfect

**Author's Note:**

> Soooo, I should have been working on my thesis or writing the next chapter of my main fic, but instead I got stessed out and wrote smut... Throw me in the sin bin!  
> Also, please leave a comment telling me what you think the 'Zemnian Cradle' is, I want to know if any of you can figure out my pervy mind XD

It was a lazy afternoon in the Xhorhaus, but of course you couldn’t tell because the sky outside was dark and starry, as always. For once, they didn’t have a mission so most of the Nein were taking advantage of the free time, shopping for supplies or just resting in their new home. It was supposed to be quality time but Jester was bored out of her mind. And she hated being bored!

She had spent a couple of hours draped over one of the library’s soft couches, drawing in her journal, letting the Traveler know about their latest adventures. It was fun for a bit, but now she was out of stories and feeling restless. And that always brought out the worst in her. She had a need for mischief.

She hopped down from the couch and started looking trough the house, trying to find any of her companions. She knew Nott and Yeza were at the market, Caduceus was taking care of his garden and Beau and Fjord were in the training room. She could go bother her roomate, but she knew Beau was so used to her shenanigans she probably wouldn’t even care. She could go look for Yasha, she was probably in her room, but the barbarian was so hard to get riled up it was almost mean to try. That left her with only one target, Caleb.

The wizard was arguably the best one to mess with, he was so quick to stammer and blush in a way that delighted her. And better yet, he was in the library too. 

With a cat-like stealthy pace that was unusual for her, she stalked trough the aisles of bookshelves, looking for the small desk, hidden in the farthest corner of the room, where Caleb usually went to read. She found him there, surrounded by books, his legs propped up on the table, eyes half-closed, caught between concentration and sleep.

“Cayyyyy-leeeeeb” She yelled in a sing-songy voice, leaping from behind a bookshelf. He jumped, startled into full consciousness, his legs falling to the floor along with his book.

“ _Mein Gott,_ Jester! You almost gave me a heart attack!”

She sat on the table in front of him, her legs swinging back and forth with child-like glee, making her poofy skirt ride up her thighs. For a second, she thought he was looking at her legs, but then he reached down and picked up his book. “Almost doesn’t count.” She gave him a wicked smile, large and fanged. “Watcha up to?”

“Reading.” he said dryly, opening the thick tome again, his eyes glue to the pages.

“Is it smut? Is that why you’re hiding in here, you’re working on your _Edubation_?” She expected him to get flustered, or to at least blush a little, but he just gave her a small smile, still not looking at her.

“ _Nein,_ it’s actually an in-depth look into the history of Asarius. Quite interesting.”

Jester fake-yawned, rolling her lavender eyes. “Sure sounds fascinating...” Her voice dripped sarcasm but he just nodded along, not seeming to notice. Feeling ignored, she reached for one of Caleb’s quills and drew a dick in one of the book covers.

“Hey, I saw that!” He finally looked up from the book, his hair falling messily over his eyes.

“No you didn’t, you were too busy ignoring me.” She pouted and he laughed. Jester knew she was being a brat but it wasn’t her fault, she was just __soooo bored__!

Slowly, he closed the book and looked at her, crossing his arms over his chest. “Alright, you have my full, undivided attention now. Speak up, woman.”

“Okay, okay, okay!” Jester hesitated, she hadn’t really thought this trough. She wanted to rile him up but now she wasn’t quite sure how, so she did the one thing that was always sure to work, awkward flirting! “Remember that smutty book you gave me about the elf girl and the Zemnian lumberjack?”

“ _Lusting Woods? Ja._ Surprisingly well written, it has some very accurate descriptions of the Zemnian mountains.”

“That’s not the part of it I was thinking about, you nerd!” She rolled her eyes again, her mischievous smile returning. “You know when he does that thing he calls the ‘Zemnian Cradle’? Is that a real thing?”

He blushed a little then, his pale neck turning a lovely shade of pink. Avoiding her eyes again, he reached for one of his books, then another, trying to focus on anything except their conversation. Jester felt a thrill of delight course trough her entire body. “ _Ja _...__ ”

“Reeeally? Does everyone in the Empire know it?” She leaned forward, her face inches away from his. “I know you’re not a lumberjack but you’re Zemnian so... are you like suuuper good at it?”

She waited for him to stammer something about her being ridiculous or avoid her question altogether. To her surprise, he did neither. “I’ve had no complaints.” He said in an even, deep voice, his eyes locked on hers. Jester felt a sudden rush of heat and her cheeks turned a deep purple.

She was used to the shy, awkward version of Caleb, the one who threw up when he was nervous and tried to blend into the crowd. It was endearing. But there was also this side of Caleb, the confident one who made walls of fire and faced the Bright Queen and looked her in the eye when talking about sex. She didn’t know how to feel about this Caleb, but she kind of liked it.

She knew he had had a complicated life before meeting them. She even knew he had a serious girlfriend once, Astrid. But now she couldn’t help but wonder exactly how sexually experienced he was. And what side of him came out in bed, the sweet, shy side, or the mysterious, confident one.

Seeing her flush though, Caleb seemed to loose his self-assurance. With quick, jerky motions, he got up and started gathering his things, his eyes cast down on the table. “But I don’t...I don’t think I’m the right person for you to talk about these things, Jester. Ask Beau... or maybe your mom?...” He tucked his books under his arm and started moving towards the door. “Anyway... The Shadowhand will be here soon, we have a Dunamancy class scheduled so I really should get going... Goodbye, Jester.”

“But...but..bye...”

She watched him walk away awkwardly, his hair shinning like fire under the light of the library’s candelabras. Had he always been this attractive? Jester knew he wasn’t bad looking, even when he was smelly and covered in dirt. She had seen woman eyeing him in Zadash and now Rosohna, even if it wasn’t as evident as it was with Fjord. But how had she not noticed how handsome he was? It was all she could think about now.

*

The next few days were confusing for Jester. Her thoughts kept wondering back to Caleb and how his brows knit together adorably when he was focused on a book, how strong his jaw looked when he shaved, how the light of his spells reflected off of his blue eyes... She was obsessed in a way she had only been with Fjord before. She wanted to draw him, she wanted to touch him... It was perplexing and overwhelming and, honestly, a little dangerous, because it kept distracting her during battles.

By the thirds night, she had had enough. Jumping out of her bed, she made her way trough the house, to the small room inside the library, Caleb’s room. She knocked on the door twice and waited. She felt ridiculous, standing there in her nightgown, he was probably asleep, she should just go back to bed. She was about to turn around when the door opened and a sleepy looking Caleb greeted her.

“Jester? What’s wrong?” He rubbed the sleep from his eyes, his voice hoarse. He was still wearing his regular clothes but his shirt was half-way unbuttoned and his hair was tied up in a bun.

“Oh I just wanted to talk... Did I wake you up? I’m sorry, I’ll come back in the morning...” She said, taking a step back.

He grabbed her wrist before she could go any further and she felt the same heat wave flow trough her. “It’s okay, I was still reading, just let sleep get the best of me for a second. Come in.”

She stepped into the cozy space, all decorated in shades of warm browns and oranges, matching Caleb perfectly. He sat down on the bed and she tried desperately not to think of how inviting the image of him on that mattress was.

“So what did you want to talk about?”

“Well...” She started hesitantly, standing by his desk, her hands grabbing anxiously at the fabric of her nightgown. “Remember the conversation we had about the ‘Zemnian Cradle’?”

“Oh no, not that again... Jester-”

“It’s not what you think!” She interrupted him, letting her words spill out before she lost her courage. “I kept thinking about what you said and how experienced you are and I was wondering if you maybe would... like if you don’t mind... maybe teach me some stuff? Not the ‘Cradle’... I don’t think I’m ready for that yet, but like other stuff...?”

He was so startle by her words he started to choke, doubling over in a coughing fit. When it stopped, he eyed her for a while, thinking over his words. “Jester... like I said before, I don’t think I’m the right person to help you with this...”

She walked over and sat next to him on the bed, feeling a little braver now that she had let it all out on the table. “You’ve kissed people before, right?” He nodded. “And you’ve _been with_ people before, right?” Another nod, this one slower, more deliberate. “Well, I haven’t even kissed anyone and I wanna learn how to do it all, the right way!”

“Didn’t you and Fjord kiss once?” He asked, his voice barely a whisper.

“That didn’t count! I was dying...I didn’t _do_ anything!” She half-yelled, her voice carrying more frustration than she even knew she felt. He laughed and some of the tension between them subsided.

“Well, you can ask him to kiss you again. Tell him to teach you...stuff...”

“Nooooo.” She shook her head vigorously, she had thought about that same idea several times and was very sure that it wasn’t a good one. “He’ll get all awkward with me... Plus, he’s had sex with Avantika and she was this super hot experienced pirate lady... I don’t want to be worse than her!”

Caleb smiled sweetly at her. “I’m sure you’ll be great.”

“How do you know? You haven’t even kissed me yet... But you could. Unless...” She let her head fall, tucking her chin against her chest, her eyes were prickling, threatening to fill up with tears of embarrassment. She started to ramble again, trying to get it all out before she actually started to cry. “Unless you don’t find me attractive... it’s okay if you don’t, I know I’m young and clumsy and loud and I have weird horns and you’re probably more into like pretty human girls and-”

He lifted her chin with his long, pale fingers, his blue eyes meeting her lavender ones in the room’s dim light. “Jester, I think you’re gorgeous.” 

She gave him a radiant smile, her tears drying up. “I sense a but coming...”

“But I think your first kiss should be special, Blueberry.” He said, but his hand traveled down to cup her cheek.

“Don’t over think it. If the Fjord thing didn’t count, than this doesn't have to count either.” _Unless you want it to,_ she added in her head. “It’s just a lesson, like when you teach Nott about magic.”

“It’s a little different.” He rolled his eyes, a hint of a smile playing at the corner of his lips.

“Pleeeeeease!” She said, pouting in the way she did whenever she needed to ask her mother to go out of the Chateaux.

“Can anybody ever say no to you?” He gave her a real smile then, his thumb rubbing circles against her cheek in a way that made her want to close her eyes and lean into it.

“It’s very rare...”

He leaned in then and Jester felt her heart skip a beat. “Are you sure, _Liebling_?” He stopped just shy of her lips, his breath tickling her skin.

“Don’t make me beg, Cayleb.” She whispered, her lips just brushing against his.

He groaned and pulled her against him. He kissed her slowly, his lips soft and sweet against hers. It was a chaste kiss but Jester felt like she was burning, his skin was so warm against hers. She wanted more, so much more of him. When he started to pull away she grabbed him by his shirt collar and pulled him back in, kissing him hard, her tongue running shyly over his bottom lip.

Caleb made a delicious sound in the back of his throat, his mouth opening to give her what she wanted. He tasted like ale and smoke and something that was uniquely Caleb, it was intoxicating. They kissed until Jester had to stop for air, her head feeling light and foggy. Caleb just stared at her as she gathered herself, his face flushed, his hair messy, fallen out if its tie.

“I... I think you’re a natural.” He stammered, his eyes heavy lidded and hazy, still taking her in like a starved man looking at his favourite meal.

“Maybe I just have a very good teacher.” She straddle his lap, pinning his legs down between her thick thighs, her nightgown ridding up to expose her soft blue skin. He looked down and this time there was no fallen book to justify his stare, his pale neck blushed a deep pink. “You can touch me if you want...”

“I really shouldn’t...”

“Oh, you _really_ should.” She grabbed his hands and put them on top of her thighs, relishing in the feeling of his warmth against her. “I prefer a more hands on teaching technique.” His hands started to roam her thighs, hesitant at first, and then more demanding, caressing her from knee to hip, making her shiver. “Tell me how to make it _extra_ good, Professor Widogast.”

“That-” He swallowed hard. “That depends on what the other person likes.”

She let one of her hand slip inside his unbuttoned shirt, feeling his burning hot skin and his racing heartbeat underneath. “Then tell me what you like.” She purred in his ear, in an imitation of the tone she had heard her mom use so often with her clients. Her voice was higher and a lot less sensual than her mother’s and, for a second, she was embarrassed that she had even tried it. But Caleb let out a strangled moan, his grip on her hips tightening, his thumbs digging into her hip bones in a way that straddled the line between pain and pleasure. She bit her lip to stop herself from moaning as well.

“That wasn’t an answer.” She licked the side of his neck, letting her fangs scrape against his skin. “Tell me, Cayleb.”

“That.” He inhaled sharply as she hit a sensitive spot between his neck and his shoulder. “B-bite me there... if-if you want to...”

That was all that direction she needed. Without hesitation, she bit down on the tender skin, licking and sucking the spot until it turned red and then purple. He whimpered and she felt his hard cock press against the inside of her thigh. 

“Was that good? I think I left a mark.” She asked, kissing the bruised skin gently. He shivered.

“ _Sehr gut, Liebling_!” He’d started breathing harder, his chest heaving against hers. “You’re a very... quick learner.”

“What should I do next?” There was a growing heat between her legs and, without even noticing, she started to grind against him. “Teach me more.”

“ _Scheisse,_ Jester! I’m a weak man, if you keep moving like that I won’t be able to hold back anymore.”

“Then don’t.” She kissed him again, nibbling on his bottom lip, her hips moving agonizingly slowly.

“Gods, I want to... I need to...” His hands were tangled in her nightgown.

“Do you want me to take this off?” She smiled wickedly, reaching for the hem of the dress.

“ _Ja...Nein?_ ” He looked so torn she almost stopped but the teasing felt too good. She laughed and then, in one smooth motion, took off her nightgown.

He stared at her naked body for the longest time, taking in her soft curves, her velvety blue skin, flushed purple down her chest and over the swells of her breasts, his lips parted, his eyes cloudy with lust.

“You’re so beautiful, _meine Liebe _.__ I must still be asleep... This has to be a dream!” He shook his head, his lovely hair falling around his face. She brushed his copper locks behind his ear, the strands impossibly soft, slipping between her fingers. She reached for the locks at his nape and pulled gently, making him groan.

“Didn’t that feel real? I’m real, Cayleb. Touch me.” 

“I can’t...” He let his head fall back, his eyes closing, his face going back to his usual pained expression. “Because if this is a dream it’ll end too soon... and if it isn’t then I’m a very selfish man. Because I want it to count. I want to be your first real kiss and I want to be the only one you think about when I touch you. ”

“Cayleb” She grabbed his face, forcing him to open his eyes again. He held his breath, bracing as if expecting her to hit him. “Let me be honest with you. This was never about anyone else. I can’t stop thinking about you lately... about kissing you, about touching you, about just making you laugh...”

“What about F-”

“Don’t say his name, this is not about him. I don’t know what I felt for him but...it’s gone now. After Avantika I realized he’s not who I thought he was. But you... the more I know about you, the more I want to be with you...”

He smiled then, sweet and a little sad. “He’s a good man, misguided but honorable. I’m a murderer and a liar and a thief... None of us deserve you, Jester, but least of all me.”

“Technically, we’ve all made mistakes, technically. What matters is that we’re trying to be better. And no one tries harder than you, Cayleb.” She kissed his cheek softly, letting her lips linger on his warm skin. “You care so much, about all of us. Let me care about you.” She whispered against his cheek.

When she pulled back his eyes were shining with unshed tears. He sighed loudly, trying to regain his composure, then he smiled. “I’m sorry I ruined your lesson.”

“Oh no, I’m not done yet, I have so much more to learn!” She crossed her arms, inadvertently pushing out her bare chest until it was precariously close to his face. “You’re not getting out of this that easily.”

“Trust me, I wasn’t trying to.” He said, blushing furiously, trying to keep eye contact. “What do you want to learn next? And please don’t say the ‘Zemnian Cradle’...”

She grinned, her fangs flashing in the candle light. She draped her arms lazily around his neck. “I wasn’t going to, but now that you mention it....”

“Jester...” He said in mock exasperation. “What about this, why don’t you tell me what __you__ like?”

“I don’t really know, really.” She shrugged, biting her lip. “But you can help me find out...”

“Alright, let me know if this is okay.” His hands slipped from her hips, up her torso and ribs. “Good?” She nodded, her breath picking up. He kissed her neck and she sighed. “Good?”

“Gods, yes!”

She could feel him smiling against her skin as he made his way down her chest, kissing every inch of her, his stubble scrapping gently against her. Then he cupped her breast with one hand, his thumb brushing her nipple ever so gently, teasing. She whimpered, leaning into his touch, desperate for more. He chuckled, his chest rumbling, making her body vibrate. It was delicious.

“That good?” He whispered.

“Yes! More, please!” She bucked against him in earnest, the heat between her legs begging for relief.

In her haze of pleasure, she didn’t even notice her tail going up to wrap itself around Caleb’s forearm. He looked at it in surprise and then caressed it gently. It was like fireworks going off behind Jester’s eyelids, the feel of it even more intense than what her clumsy grinding provided. She couldn’t stop the loud moan that escaped her lips.

“Oh, looks like I also have a lot to learn about... like tiefling anatomy.”

“I’m so sorry!” She said, quickly unwrapping her tail. “Was that weird?”

“ _Nein, Schatz._ ” He grabbed her tail before she could tuck it away behind her, his skillful fingers massaging its length, making her whimper. “Just surprising. Never apologize for something that makes you feel good.”

Still working her tail, he took her breast into his mouth, nipping at her skin, sucking on her nipple, his tongue doing slow circles around it. Jester felt like she was shattering, falling apart under his touch. Every inch of her body was hyper-sensitive, but nowhere more than between her legs. The ache was maddening, both deliciously sweet and agonizing, like an emptiness she had never felt before.

“Cayleb, please, I need you so much, it hurts!” She said, half coherent, trying desperately to find a rhythm with her hips. “ _Please_ , fuck me Cayleb.”

He let out a guttural sound, half moan, half growl. It was primal and territorial and it made Jester’s heart jump in her chest. But then he let go of her tail and she felt like screaming. With a strength Jester never thought he had, he grabbed her by the waist and flipped them around, leaving her laying on his bed while he stood over her.

“That’s a lesson for another day. You need to take it slowly, Blueberry. But don’t worry, I’ll take care of you.”

She wanted to protest, but he stopped her with a kiss, the weight of his body pressing her down against the mattress. His hand trailed down her body until it reached the patch of soft navy curls between her legs and she gasped, her legs opening wider for him. He circled her clit and then dipped lower, letting a single finger enter her with ease.

“ _Scheisse,_ Jessie, you’re so wet...so tight...”

“I told you I needed you.” She moaned as he moved inside her, slowly and gently, very aware of the fact that she was a virgin, the heel of his hand grinding against her clit.

“Tell me if it hurts, _Liebling._ ” He added another finger and she tensed around him, her sharp teeth biting down on her lower lip. “Do you want me to stop?”

“Fuuuuuck!” She screamed as he started to pull away, her eyes rolling back in her head. “Don’t you dare!”

He chuckled and she took the chance to inch her hand down his body until she could palm him trough his pants. He froze.

“Jester...”

“Shhh, I told you not to stop.” She wrapped her tail around his wrist, keeping him in place, inside her, as she started to rub the bulge in his pants.

“You don’t have to...” He groaned, the feeling of her hand trough the fabric incredibly intense but also not enough.

“I want to.” She kissed him slowly, reassuringly. His fingers started to move again. “Professor, may I take off your pants?” She asked, her voice going a little breathy as he hit a particularly sensitive spot inside her.

He nodded, not trusting his voice at the moment and she started to unlace the front of his trousers. He let out a low hiss of pleasure as she took him in her hand, her small palm struggling to close around him, he was surprisingly big and _oh_ so warm. Not for the first time that night, she wished his self control wasn’t as good.

They worked almost in unison, each pump of her fist equaled by the motion of his fingers, but when he curled them inside her, hitting that specific spot again, Jester knew she wouldn’t last long.

“Cayleb, I think I...”

“ _Cum for me, Schatz._ ” He whispered against her skin, his tone low and demanding.

That was all it took. Her hand never stopping, she gave in to the growing pressure building inside her until it reached its climax. Her vision went white, her entire body tensing and then spasming as waves of pleasure hit her time and time again. As she trembled, he came in her palm, his body shaking like hers as he held her close.

When it was over, they laid in bed next to each other, Caleb’s body cradling her from behind, his arm around her waist, his face hidden in the crook of her neck. For a long time, they just laid there in silence, hearing their racing breaths and feeling their heartbeats calm down. All the while, Jester couldn’t stop smiling, she had never felt more full of love.

“That was... even better than the books said.”

“Did it satisfy your thirst for knowledge?” He kissed her neck, his arm tightening around her.

“Oh no, not at all! In fact, it showed me that I absolutely need to learn more!” He laughed, his breath tickling her neck. “I think we should have another lesson in the morning!”

“That soon?” 

“Of course, didn’t you ever hear that practice makes perfect? And besides, you still haven’t taught me the ‘Cradle’ so...”

“You’re incorrigible.”

“Yes, but you love that about me.” She turned around and kissed him tenderly, her body pressed against his.

“You’re not wrong.”


End file.
